During the Gran Canaria Desktop Summit, Richard M. Stallman of the Free Software Foundation (and the Superfluous Introduction Award goes to...) gave a keynote speech. Said keynote speech raised a few eyebrows in the Free software community because of a number of questionable remarks regarding women in technology. David "Lefty" Schlesinger, member of the GNOME Advisory Board and active in the mobile open source community, took issue with RMS' remarks and decided to call him out on it. The response he got was... Less than satisfying.

You say "it's all about timing", and I ask: "Who's timing"? Yours? What is "inappropriate"? Who told you so? Did you make that decision on your own? Did your parents teach you? What makes it right/true? What is true? What is right?

It's all very simple. It has nothing to do with right/wrong, true/false or any sort of absolute terms. It's all about reactions from your audience. Did you get the reaction you wanted from your audience? Did the audience get the message your where trying to convey? Has the audiences opinion of you changed in the way you wanted?

I am not preaching relativism, but "anybody with any social awareness" only holds water locally, that is, it's specific to social contexts like culture.

Which is why you change your behavior to fit the culture and local context in which you are. A big part of social awareness is to be aware of the local context you are in and adjusting your behavior on the fly. The same message delivered the same way will get you vastly different responses depending on where you are. This should be obvious to most people. It takes only a little bit more awareness to predict that response.

I behave differently when I'm at a pub with close friends than if I'd be discussing business with possible future clients at a nice restaurant. Jokes that I'd happily tell in one setting I wouldn't tell in the other, due to the different cultural and social context.

himself why people will try to restrict others' freedom of speech at every opportunity

Nobody is trying to restrict anybodies free speech. It's not about what you are allowed to say. Just because I criticize your message and how you delivered it does not mean I'm criticizing your right to free speech.